Sag Harbor Village has hired one contractor for two waterfront jobs, and both are timed for the off-season. Chesterfield Associates holds a $2,146,410 contract to replace A Dock at the village marina and a $1,032,070 contract to build a boardwalk linking Windmill Beach to John Steinbeck Waterfront Park. Together that comes to about $3.18 million in work along the shoreline at the foot of Main Street.
The design choices point in one direction. The railing on the new dock was swapped for a version that keeps the harbor view. The boardwalk will be fully ADA-compliant. The next phase is meant to spare boat owners the wade out to their moorings. A later phase would extend a walking path west along West Water Street. Each choice favors people who reach the water on foot, and nearly all of the work is scheduled for the months when the fewest people are there to see it.
What Is Underway, and Where It Stands
| Project | Location | Contract | Status as of mid-October 2026 |
|---|---|---|---|
| A Dock replacement | 11 West Water Street, west of The Beacon | $2,146,410, Chesterfield Associates | Awarded; work expected to start early November |
| Steinbeck Park boardwalk | 6 Ferry Road, Windmill Beach to Steinbeck Park | $1,032,070, Chesterfield Associates | Awarded; construction estimated for this fall, start date not yet reported |
| Rest of marine facility, including the floating docks replacing the cable moorings | 11 West Water Street | Separate bid still to come | DEC permit received mid-June; Army Corps permit still pending as of July |
| West Water Street bulkhead and path | Marine Park toward Cilli Farm | None | Still in planning |
The Village Board's June 18, 2026 special-meeting agenda listed a resolution to award the A Dock contract to Chesterfield. By the Harbor Committee's July 2 meeting, the project engineer confirmed the bid had gone to Chesterfield. The village's notice to bidders for the Steinbeck boardwalk went out July 2, 2026, with sealed bids due July 20, so a fall start fits the schedule.
A Dock Comes Out After the Boats Do
A Dock has been due for replacement for years. It is a T-shaped municipal pier with 20 slips, and it sits just west of The Beacon restaurant. In late 2025, Trustee Jeanne Kane, who oversees the waterfront for the Village Board, told the Sag Harbor Express on 27east that the dock:
"was built in the 1970s and on its last legs. That's why we are so anxious to get it replaced as soon as possible."
The same report explained why the work did not happen last winter. The state Department of Environmental Conservation permit came too late to bid and finish the job before boats returned, and the qualified marine contractors were already booked. Kane said the project would likely start in early November 2026 and finish by late March. Later Harbor Committee coverage confirmed an early-November start "at the end of boating season," with the new dock system meant to be ready for boats on April 1, 2027.
The old pier will be replaced with a floating dock, a new bulkhead, and a new boardwalk and catwalk. When the wetlands permit was first approved, the plan called for a timber railing. The village replaced it with timber piles, which still protect pedestrians but keep the view and the look of the area in a way the railing would not have. In other words, a dock built for boats was redesigned partly around what a person standing on West Water Street will see.
The Boardwalk That Runs Under the Bridge
The second contract follows the same priorities on the other side of Long Wharf. The boardwalk will connect Windmill Beach, just off Long Wharf, to John Steinbeck Waterfront Park on the far side of the Lance Corporal Jordan Haerter Veterans Memorial Bridge. It will be 8 feet wide and built on piles on the land side of the existing bulkhead. A 400-square-foot gravel section under the bridge on Ferry Road joins the two halves. Twelve timber benches will be set in pairs along the stretch near the windmill.
According to the 27east report on the contract award, the walkway will be fully ADA-compliant. The landscape plan for Steinbeck Park and Windmill Beach, along with its upkeep, was provided free of charge by local landscape architect Ed Hollander. Former Mayor Jim LaRocca first championed the idea of linking the two waterfront areas, and Mayor Tom Gardella has kept it a central priority. Grants cover most of the cost and village funds cover the rest.
The boardwalk has been slow to arrive. In November 2024, the East Hampton Star reported that early ecological work had begun and that the boardwalk was expected by early spring 2025. That date has passed, and the current schedule only says construction is "estimated to begin this fall." No source has yet reported a groundbreaking or announced closures of Windmill Beach, Long Wharf parking or Steinbeck Park during the work.
Why the Moorings Are Next
The marina plan goes beyond A Dock. The village also wants to remove the cable mooring system nearby, which has room for 43 small boats, and replace it with floating docks. Kane said the cable system has been losing popularity: only 32 boats used it in the season before her comments. Part of the reason, she said, is that owners often have to wade through the water to reach their boats. Floating docks would end that.
That phase is further behind. At its July 2 meeting, the Harbor Committee approved a wetlands permit for the larger marine facility project at 11 West Water Street. The project includes removing mooring piles and water-access staircases, adding a new floating dock and boardwalk, and building an electric service platform. The committee could vote only because the DEC permit had arrived in mid-June. The village still needs an Army Corps of Engineers permit before it can put that work out to bid. Matt Jedlicka of the engineering firm LKMA told the Sag Harbor Express that A Dock would likely start in the fall. On the rest of the facility, he said, "Maybe we'll be able to get it started over the winter and ready for next year," depending on whether the village has the funds this year.
The village had already approved borrowing up to $4 million to cover A Dock, the cable-system replacement and the boardwalk together. That is a ceiling for all three projects, not the price of any single one.
The Walk West of Marine Park Is Still a Plan
The phase that would do the most for walkers is also the least developed. Kane described a third step: a bulkhead along West Water Street to support the village's effort to build a pedestrian path from Marine Park to the Cilli Farm property. Southampton Town and Suffolk County co-own Cilli Farm, and the village has been working on an agreement with them to create trails there. No current report sets a schedule. If the boardwalk and the marina work both finish, a walk from Steinbeck Park west along the harbor to Marine Park will be built, and this path would extend it further.
At the Corner of Main Street, the Spaces Are in Flux
On the commercial side of the waterfront, the two addresses closest to the water are both changing hands or uses, and the owners of both have said they want full-time or year-round operators.
As the Sag Harbor Express reported, on September 3 Kelly and John Piccinnini said they would not open The Corner at 1 Main Street. The property's owner group said it wanted a new full-time tenant or operator in place by spring 2027, or sooner.
Nearby, Cruust opened in July in the former Espresso da Asporto space on the cove. Manager Bobby Deery told Express Magazine that the shop's winter focus is consistency, community feedback and refining the menu. According to Sag Harbor Express coverage of the Planning Board, that address, 2 Main Street, is one of two properties in a proposed Mavik Capital redevelopment with 22 Long Island Avenue. The plan calls for three retail stores and three restaurants. Its representatives have said they would give priority to retail tenants who commit to operating year-round. The proposal is at an early stage and still needs variances and environmental review. The Planning Board resumes its review on October 27 at 5 p.m.
Key Dates Through April
- October 27, 5 p.m. The Planning Board resumes its review of the 2 Main Street and 22 Long Island Avenue proposal.
- This fall, date not yet reported. Expected start of the Steinbeck Park boardwalk, under the village's current estimate.
- Early November. Expected start of A Dock demolition and rebuilding, once the boats are out.
- Late March. Kane's target for finishing the marina work.
- April 1, 2027. Planned date for boats to start using the new A Dock system.
- Spring 2027, or sooner. The owner group's target for a new full-time tenant at 1 Main Street.
The waterfront projects on this list need wetlands permits, approvals from more than one agency, and construction windows set by the boating season. We follow those same factors on any harbor-side property, from bulkhead condition to how far the permits have advanced. If you own along Sag Harbor's waterfront and want to understand how this winter's work could affect your property, Heskell Advisors can schedule a confidential market consultation.
